Insecure 10th Anniversary Tour 2026: Issa Rae & Prentice Penny Dates & Tickets
- Capital City Tickets
- 1 day ago
- 3 min read
Issa Rae and showrunner Prentice Penny are hitting the road to celebrate 10 years of the groundbreaking HBO series Insecure. The Insecure: The 10th Anniversary Tour is a 13-city live conversation tour featuring candid stories, behind-the-scenes moments, episode breakdowns, and special guest appearances from cast members like Yvonne Orji, Jay Ellis, and Natasha Rothwell on select dates. Insecure 10th Anniversary Tour 2026!
This intimate theater tour (not a traditional concert) offers fans a once-in-a-lifetime chance to relive the iconic moments, friendships, and cultural impact of the show that defined a generation. Tickets are on sale now with presales active — here’s everything you need to know about dates, venues, how to get cheap tickets, and more.
Insecure: The 10th Anniversary Tour 2026 – Full Dates
Here is the complete list of announced dates and venues:
September 10, 2026 – Philadelphia, PA – The Met Philadelphia
September 11, 2026 – Washington, DC – The Theater at MGM National Harbor
September 13, 2026 – Detroit, MI – The Fillmore Detroit
September 16, 2026 – Boston, MA – MGM Music Hall at Fenway
September 17, 2026 – Brooklyn, NY – Brooklyn Paramount
September 18, 2026 – Montclair, NJ – The Wellmont Theater
September 25, 2026 – Las Vegas, NV – Palazzo Theatre
September 26, 2026 – Oakland, CA – Fox Theatre
October 1, 2026 – Chicago, IL – The Chicago Theatre
October 2, 2026 – Atlanta, GA – Tabernacle
October 3, 2026 – Irving, TX – The Pavilion at Toyota Music Factory
October 4, 2026 – Houston, TX – Bayou Music Center
October 8, 2026 – Inglewood, CA – YouTube Theater
Special Guests: Yvonne Orji, Jay Ellis, and Natasha Rothwell will appear on select dates (check individual show listings for confirmation).
Presale & Ticket Information
Citi Presale: Started July 15, 2026 (use your Citi card for early access)
General On-Sale: July 16, 2026 at 12:00 p.m. local time via Ticketmaster
Tickets are available now on Ticketmaster, Live Nation, and venue websites.
Pro Tip: Act fast — these theater events are expected to sell out quickly in major markets like New York, Chicago, Atlanta, and Los Angeles.
How to Get Cheap Insecure 10th Anniversary Tour Tickets
Here are the best ways to save money:
Compare prices across Ticketmaster, SeatGeek, Capital City Tickets, and StubHub.
Use price alerts for your preferred city.
Look for group discounts (many theaters offer deals for 10+ tickets).
Stack promotions where possible (credit card offers, fan club access, or early-bird deals).
Consider upper-level or side seats for the best value.
Buy during presale windows to avoid resale markups.
Current prices vary by city and seat location but are generally more affordable than major concert tours since these are theater events.
Insecure & Issa Rae FAQ - Insecure 10th Anniversary Tour 2026
What is the Insecure 10th Anniversary Tour? A live, conversational tour co-hosted by Issa Rae (creator/star) and Prentice Penny (showrunner). Expect untold stories, behind-the-scenes insights, episode breakdowns, audience Q&A, and special cast appearances.
Who is Issa Rae? Issa Rae is an Emmy-nominated actress, writer, producer, and creator of the hit HBO series Insecure (2016–2021). She’s also known for her work in film, producing, and her memoir .
What was Insecure about? The groundbreaking HBO comedy followed Issa Dee (played by Rae) navigating life, love, friendship, and career in Los Angeles alongside her best friend Molly (Yvonne Orji). The show was praised for its authentic portrayal of Black millennial experiences.
Will all cast members appear on every date? No — core hosts are Issa Rae and Prentice Penny. Select cast members (Yvonne Orji, Jay Ellis, Natasha Rothwell, etc.) will appear on specific dates only.
Is this a concert or a show? It’s a live theatrical event with conversation, storytelling, and interaction — not a musical performance.
Are there more dates being added? Additional stops are possible. Check Ticketmaster regularly for updates.
Final Tips
This tour is a rare opportunity to celebrate one of television’s most beloved series with the people who made it happen. Whether you’re a longtime fan or discovering Insecure for the first time, these dates promise laughter, nostalgia, and unforgettable moments.
Important Disclaimer: We are an independent ticket news and guide site and are not affiliated with Issa Rae, Prentice Penny, HBO, Live Nation, Ticketmaster, or any venue. Ticket prices and availability are subject to change. Always purchase from official or trusted resale platforms. Resale tickets may exceed face value.
Ready to relive Insecure? Which city are you hoping to attend? Drop it in the comments!